title: Antimicrobial activity of imidazo[1,5-a]quinoxaline derivatives with pyridinium moiety.
abstract: 3-Phenyl(methyl)-5-alkyl-1-(pyridin-3-yl)imidazo[1,5-a]quinoxalin-4-ones (2a-f) and their N-alkyl-pyridinium salts (3a-o), including 1,n-bis{3-(3-phenylimidazo[1,5-a]quinoxalin-4(5H)-on-1-yl)pyridinium}alkane dibromides (4a-d, 5, 6) have been synthesized. It has been established that the antimicrobial properties of imidazo[1,5-a]quinoxaline derivatives are connected with the presence of various alkyl substituents in the position 1 of the pyridine ring and in the position 5 of the imidazo[1,5-a]quinoxaline system. Chlorides and iodides are more active towards bacteria than fungi. Compounds 3d, 3e, 3m and 3n showed an effective bacteriostatic activity. Compound showed not only well defined bacteriostatic activities but also good fungistatic activities, with the MIC values comparable with the reference drugs. Toxicity of more effective (imidazo[1,5-a]quinoxalin-4-on-1-yl)-1-pyridinium halides was examined in mice.
authors.affiliation: AE Arbuzov Institute of Organic and Physical Chemistry of Russian Academy of Sciences, Arbuzov Str. 8, Kazan 420088, Russian Federation.
authors.forename: Alexey A
authors.initials: AA
authors.lastname: Kalinin
authors.forename: Alexandra D
authors.initials: AD
authors.lastname: Voloshina
authors.forename: Nataliya V
authors.initials: NV
authors.lastname: Kulik
authors.forename: Vladimir V
authors.initials: VV
authors.lastname: Zobov
authors.forename: Vakhid A
authors.initials: VA
authors.lastname: Mamedov
mesh_terms: D000818:Animals; D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology* / Q000633:toxicity; D001419:Bacteria / Q000187:drug effects; D015195:Drug Design; D005260:Female; D005658:Fungi / Q000187:drug effects; D007093:Imidazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology* / Q000633:toxicity; D008297:Male; D051379:Mice; D008826:Microbial Sensitivity Tests; D011726:Pyridinium Compounds / Q000737:chemistry*
chemical_list: D000890:Anti-Infective Agents; D007093:Imidazoles; D011726:Pyridinium Compounds
keywords: Bacteriostatic activity; Fungistatic activity; Imidazo[1,5-a]quinoxalines; LQMYQAIQGKKQPJ-UHFFFAOYSA-N; OKDNNAUBBAPRBR-UHFFFAOYSA-N; Pyridinium salt